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Volumn 17, Issue 13, 2006, Pages 1931-1936

Asymmetric ring opening of meso-epoxides with B-halobis(2-isocaranyl)boranes 2-dIcr2BX

Author keywords

[No Author keywords available]

Indexed keywords

2,3 BUTENE OXIDE; BORANE DERIVATIVE; CYCLOHEXANE OXIDE; CYCLOPENTENE OXIDE; EPOXIDE; OXIDE; REAGENT; UNCLASSIFIED DRUG;

EID: 33746956115     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2006.06.044     Document Type: Article
Times cited : (15)

References (45)
  • 1
    • 0026080791 scopus 로고
    • and pertinent references therein
    • Narasaka K. Synthesis 39 (1991) 1 and pertinent references therein
    • (1991) Synthesis , vol.39 , pp. 1
    • Narasaka, K.1
  • 24
    • 0028196798 scopus 로고
    • and references cited therein
    • Bonini C., and Righi G. Synthesis (1994) 225 and references cited therein
    • (1994) Synthesis , pp. 225
    • Bonini, C.1    Righi, G.2
  • 39
    • 33747007182 scopus 로고    scopus 로고
    • Roy, C. D.; Brown, H. C. Presented in H. C. Brown Lectures in Chemistry (1999), Purdue University, IN, USA.
  • 41
    • 33746985033 scopus 로고    scopus 로고
    • note
    • 11B NMR (2-3 d). The resulting boronate was then treated with diethanolamine (5 mmol) to retrieve the 2-chlorocyclohexan-1-ol. The crude product was purified on silica gel column chromatography (5-10% ethyl ether in n-hexanes or n-pentane) and the enantiomeric excess (ee) was determined by HPLC analysis on a Daicel Chiralcel OD-H column after transforming the 2-chlorocyclohexan-1-ol into both 3,5-dinitrobenzoyl- and 1-naphthoyl esters. Enatiomeric excess: 78% (1S,2S).
  • 44
    • 18244385266 scopus 로고    scopus 로고
    • 2 (Paper withdrawn, Buono, G. Angew. Chem., Int. Ed. 2001, 40, 4536; Buono, G. Eur. J. Org. Chem. 2002, 218).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.